NPASS Compound

Structure

CID272907 OpenBabel06191716082D 24 27 0 0 1 0 0 0 0 0999 V2000 5.5018 0.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6787 1.8969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6802 1.1583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8598 0.6451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3736 -0.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2356 -0.0175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9869 -1.1073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9912 0.9527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9758 -0.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6711 0.9332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8327 0.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1421 0.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1344 -0.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8250 -0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3837 1.0858 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4303 0.8762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2353 0.0433 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4166 -0.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6767 0.2516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3665 -1.1073 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6557 -1.0066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5924 1.9681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1542 -1.5872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 19 1 0 0 0 0 8 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 11 14 2 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 6 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 20 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 20 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	344.865
LogP:	3.493
LogD:	3.261
LogS:	-3.891
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	4.995
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	2.3569698896608315e-05
Pgp-inhibitor:	0.147
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.821
Plasma Protein Binding (PPB):	95.48712921142578%
Volume Distribution (VD):	0.814
Pgp-substrate:	6.672650337219238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.717
CYP2C19-inhibitor:	0.357
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.512
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.575
CYP2D6-substrate:	0.53
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.465

ADMET: Excretion

Clearance (CL):	1.9
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.352
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.478
Maximum Recommended Daily Dose:	0.707
Skin Sensitization:	0.493
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.094
Respiratory Toxicity:	0.852

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC272907

Natural Product ID:	NPC272907
*Common Name:**	WTPQRFSKUFBXKY-WWNBULGVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WTPQRFSKUFBXKY-WWNBULGVSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-10(2)11-8-12-13(9-14(11)21)20-7-5-6-19(3,4)17(20)16(15(12)22)24-18(20)23/h8-10,15-17,21-22H,5-7H2,1-4H3/t15-,16-,17+,20+/m1/s1
SMILES:	CC(C)c1cc2c(cc1O)[C@@]13CCCC(C)(C)[C@@H]1[C@@H]([C@@H]2O)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651063
PubChem CID:	50900505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6000.0	nM	PMID[469600]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[469600]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[469600]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[469600]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[469600]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC272907 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1092
0.2-0.3	2565
0.3-0.4	4783
0.4-0.5	9920
0.5-0.6	9175
0.6-0.7	11156
0.7-0.8	3583
0.8-0.85	119
0.85-0.9	15
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC2681
0.9638	High Similarity	NPC126707
0.9489	High Similarity	NPC3218
0.9362	High Similarity	NPC191899
0.9362	High Similarity	NPC246229
0.9118	High Similarity	NPC49742
0.9091	High Similarity	NPC474991
0.9028	High Similarity	NPC127046
0.8913	High Similarity	NPC293454
0.8897	High Similarity	NPC5568
0.8889	High Similarity	NPC84786
0.8699	High Similarity	NPC58752
0.8639	High Similarity	NPC470757
0.8593	High Similarity	NPC181334
0.8581	High Similarity	NPC471852
0.8561	High Similarity	NPC291001
0.8552	High Similarity	NPC248068
0.8542	High Similarity	NPC471853
0.8529	High Similarity	NPC87985
0.8529	High Similarity	NPC137750
0.8511	High Similarity	NPC213122
0.8507	High Similarity	NPC249340
0.8507	High Similarity	NPC162935
0.8503	High Similarity	NPC75295
0.8493	Intermediate Similarity	NPC477207
0.8456	Intermediate Similarity	NPC477206
0.8446	Intermediate Similarity	NPC63918
0.8444	Intermediate Similarity	NPC121168
0.8421	Intermediate Similarity	NPC62051
0.8406	Intermediate Similarity	NPC471077
0.84	Intermediate Similarity	NPC142654
0.8382	Intermediate Similarity	NPC471187
0.838	Intermediate Similarity	NPC202225
0.8378	Intermediate Similarity	NPC258856
0.8369	Intermediate Similarity	NPC165612
0.8367	Intermediate Similarity	NPC100242
0.8358	Intermediate Similarity	NPC478121
0.8333	Intermediate Similarity	NPC475957
0.8333	Intermediate Similarity	NPC474945
0.8333	Intermediate Similarity	NPC477592
0.8333	Intermediate Similarity	NPC476022
0.831	Intermediate Similarity	NPC476282
0.831	Intermediate Similarity	NPC78307
0.8309	Intermediate Similarity	NPC11250
0.8299	Intermediate Similarity	NPC184935
0.8298	Intermediate Similarity	NPC476847
0.8298	Intermediate Similarity	NPC471851
0.8296	Intermediate Similarity	NPC241001
0.8289	Intermediate Similarity	NPC124842
0.8267	Intermediate Similarity	NPC166583
0.8267	Intermediate Similarity	NPC53362
0.8255	Intermediate Similarity	NPC170055
0.8235	Intermediate Similarity	NPC178574
0.8235	Intermediate Similarity	NPC369
0.8235	Intermediate Similarity	NPC65591
0.8235	Intermediate Similarity	NPC293831
0.8222	Intermediate Similarity	NPC234337
0.8222	Intermediate Similarity	NPC183339
0.8222	Intermediate Similarity	NPC133389
0.8212	Intermediate Similarity	NPC94781
0.8209	Intermediate Similarity	NPC471671
0.8205	Intermediate Similarity	NPC470339
0.8205	Intermediate Similarity	NPC314795
0.8201	Intermediate Similarity	NPC474944
0.8201	Intermediate Similarity	NPC253681
0.82	Intermediate Similarity	NPC285122
0.8194	Intermediate Similarity	NPC279463
0.8188	Intermediate Similarity	NPC84568
0.8188	Intermediate Similarity	NPC300684
0.8188	Intermediate Similarity	NPC218866
0.8188	Intermediate Similarity	NPC260152
0.8188	Intermediate Similarity	NPC48130
0.8182	Intermediate Similarity	NPC111845
0.8182	Intermediate Similarity	NPC209393
0.8182	Intermediate Similarity	NPC205172
0.8176	Intermediate Similarity	NPC308572
0.817	Intermediate Similarity	NPC205918
0.8169	Intermediate Similarity	NPC243305
0.8169	Intermediate Similarity	NPC312341
0.8163	Intermediate Similarity	NPC475907
0.8163	Intermediate Similarity	NPC304110
0.8163	Intermediate Similarity	NPC29599
0.8163	Intermediate Similarity	NPC27518
0.8158	Intermediate Similarity	NPC303989
0.8158	Intermediate Similarity	NPC478219
0.8158	Intermediate Similarity	NPC327962
0.8158	Intermediate Similarity	NPC280753
0.8158	Intermediate Similarity	NPC247219
0.8158	Intermediate Similarity	NPC44378
0.8156	Intermediate Similarity	NPC131684
0.8153	Intermediate Similarity	NPC472055
0.8153	Intermediate Similarity	NPC21046
0.8151	Intermediate Similarity	NPC230811
0.8151	Intermediate Similarity	NPC477593
0.8148	Intermediate Similarity	NPC42657
0.8148	Intermediate Similarity	NPC469644
0.8146	Intermediate Similarity	NPC81835
0.8143	Intermediate Similarity	NPC69424
0.8143	Intermediate Similarity	NPC84672
0.8143	Intermediate Similarity	NPC78364
0.8143	Intermediate Similarity	NPC176130
0.8141	Intermediate Similarity	NPC143328
0.8134	Intermediate Similarity	NPC304510
0.8134	Intermediate Similarity	NPC172219
0.8133	Intermediate Similarity	NPC470038
0.8129	Intermediate Similarity	NPC192219
0.8129	Intermediate Similarity	NPC174599
0.8129	Intermediate Similarity	NPC3449
0.8129	Intermediate Similarity	NPC124030
0.8129	Intermediate Similarity	NPC82190
0.8129	Intermediate Similarity	NPC471456
0.8125	Intermediate Similarity	NPC194970
0.8125	Intermediate Similarity	NPC255787
0.8125	Intermediate Similarity	NPC477594
0.8121	Intermediate Similarity	NPC25491
0.8116	Intermediate Similarity	NPC198014
0.8112	Intermediate Similarity	NPC476389
0.8108	Intermediate Similarity	NPC477595
0.8102	Intermediate Similarity	NPC253627
0.8101	Intermediate Similarity	NPC477627
0.8099	Intermediate Similarity	NPC108129
0.8092	Intermediate Similarity	NPC279442
0.8089	Intermediate Similarity	NPC472299
0.8089	Intermediate Similarity	NPC4950
0.8089	Intermediate Similarity	NPC218818
0.8085	Intermediate Similarity	NPC476024
0.8085	Intermediate Similarity	NPC229894
0.8085	Intermediate Similarity	NPC3009
0.8082	Intermediate Similarity	NPC119542
0.8079	Intermediate Similarity	NPC120536
0.8077	Intermediate Similarity	NPC283480
0.8077	Intermediate Similarity	NPC10945
0.8077	Intermediate Similarity	NPC148323
0.8077	Intermediate Similarity	NPC478223
0.8075	Intermediate Similarity	NPC473094
0.8071	Intermediate Similarity	NPC325294
0.8071	Intermediate Similarity	NPC321822
0.8069	Intermediate Similarity	NPC477596
0.8069	Intermediate Similarity	NPC153088
0.8069	Intermediate Similarity	NPC103082
0.8067	Intermediate Similarity	NPC471305
0.8063	Intermediate Similarity	NPC41689
0.806	Intermediate Similarity	NPC38893
0.806	Intermediate Similarity	NPC308311
0.806	Intermediate Similarity	NPC477137
0.8058	Intermediate Similarity	NPC85565
0.8056	Intermediate Similarity	NPC477139
0.8056	Intermediate Similarity	NPC138472
0.8043	Intermediate Similarity	NPC182333
0.8043	Intermediate Similarity	NPC478058
0.8043	Intermediate Similarity	NPC471794
0.8043	Intermediate Similarity	NPC176208
0.8043	Intermediate Similarity	NPC273336
0.8042	Intermediate Similarity	NPC18798
0.8042	Intermediate Similarity	NPC78575
0.8041	Intermediate Similarity	NPC470035
0.8041	Intermediate Similarity	NPC476534
0.8041	Intermediate Similarity	NPC168471
0.8041	Intermediate Similarity	NPC315578
0.8041	Intermediate Similarity	NPC172311
0.8041	Intermediate Similarity	NPC327187
0.8039	Intermediate Similarity	NPC474310
0.8039	Intermediate Similarity	NPC116292
0.8039	Intermediate Similarity	NPC267469
0.8039	Intermediate Similarity	NPC179128
0.8039	Intermediate Similarity	NPC87630
0.8029	Intermediate Similarity	NPC164852
0.8029	Intermediate Similarity	NPC32322
0.8029	Intermediate Similarity	NPC259703
0.8028	Intermediate Similarity	NPC276238
0.8028	Intermediate Similarity	NPC117899
0.8026	Intermediate Similarity	NPC477483
0.8026	Intermediate Similarity	NPC66991
0.8026	Intermediate Similarity	NPC325032
0.8025	Intermediate Similarity	NPC473095
0.8025	Intermediate Similarity	NPC208651
0.8025	Intermediate Similarity	NPC206641
0.8025	Intermediate Similarity	NPC473096
0.8014	Intermediate Similarity	NPC475111
0.8014	Intermediate Similarity	NPC72667
0.8014	Intermediate Similarity	NPC30491
0.8014	Intermediate Similarity	NPC262936
0.8014	Intermediate Similarity	NPC326847
0.8013	Intermediate Similarity	NPC320734
0.8013	Intermediate Similarity	NPC472807
0.8013	Intermediate Similarity	NPC474501
0.8013	Intermediate Similarity	NPC478160
0.8012	Intermediate Similarity	NPC200726
0.8012	Intermediate Similarity	NPC472621
0.8012	Intermediate Similarity	NPC469419
0.8	Intermediate Similarity	NPC21873
0.8	Intermediate Similarity	NPC477893
0.8	Intermediate Similarity	NPC471731
0.8	Intermediate Similarity	NPC159721
0.8	Intermediate Similarity	NPC477896
0.8	Intermediate Similarity	NPC204582
0.7987	Intermediate Similarity	NPC261659
0.7987	Intermediate Similarity	NPC470037
0.7987	Intermediate Similarity	NPC266365
0.7987	Intermediate Similarity	NPC225854

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC272907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	725
0.2-0.3	1540
0.3-0.4	2564
0.4-0.5	2272
0.5-0.6	1191
0.6-0.7	554
0.7-0.8	67
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8169	Intermediate Similarity	NPD6663	Approved
0.8143	Intermediate Similarity	NPD5736	Approved
0.7895	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD37	Approved
0.7867	Intermediate Similarity	NPD4628	Phase 3
0.7862	Intermediate Similarity	NPD6234	Discontinued
0.7848	Intermediate Similarity	NPD4966	Approved
0.7848	Intermediate Similarity	NPD4965	Approved
0.7848	Intermediate Similarity	NPD4967	Phase 2
0.7826	Intermediate Similarity	NPD3019	Approved
0.7748	Intermediate Similarity	NPD8166	Discontinued
0.7714	Intermediate Similarity	NPD3092	Approved
0.7698	Intermediate Similarity	NPD2932	Approved
0.7662	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2533	Approved
0.7662	Intermediate Similarity	NPD2534	Approved
0.7662	Intermediate Similarity	NPD2532	Approved
0.7636	Intermediate Similarity	NPD7228	Approved
0.7622	Intermediate Similarity	NPD3094	Phase 2
0.7607	Intermediate Similarity	NPD6232	Discontinued
0.7603	Intermediate Similarity	NPD3764	Approved
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7582	Intermediate Similarity	NPD6190	Approved
0.7576	Intermediate Similarity	NPD7473	Discontinued
0.7554	Intermediate Similarity	NPD3091	Approved
0.7546	Intermediate Similarity	NPD7199	Phase 2
0.7533	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2629	Approved
0.75	Intermediate Similarity	NPD4060	Phase 1
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5404	Approved
0.7483	Intermediate Similarity	NPD5405	Approved
0.7483	Intermediate Similarity	NPD5408	Approved
0.7483	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7442	Intermediate Similarity	NPD8150	Discontinued
0.7431	Intermediate Similarity	NPD1283	Approved
0.7415	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7003	Approved
0.7394	Intermediate Similarity	NPD3023	Approved
0.7394	Intermediate Similarity	NPD3026	Approved
0.7389	Intermediate Similarity	NPD6273	Approved
0.7384	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3620	Phase 2
0.7383	Intermediate Similarity	NPD4140	Approved
0.7376	Intermediate Similarity	NPD3025	Approved
0.7376	Intermediate Similarity	NPD3024	Approved
0.7368	Intermediate Similarity	NPD2438	Suspended
0.7368	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD6100	Approved
0.7349	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD8127	Discontinued
0.7324	Intermediate Similarity	NPD3095	Discontinued
0.732	Intermediate Similarity	NPD5762	Approved
0.732	Intermediate Similarity	NPD5763	Approved
0.729	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4110	Phase 3
0.729	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2979	Phase 3
0.7261	Intermediate Similarity	NPD7390	Discontinued
0.726	Intermediate Similarity	NPD1470	Approved
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7240	Approved
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3226	Approved
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD1281	Approved
0.7222	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD230	Phase 1
0.72	Intermediate Similarity	NPD8032	Phase 2
0.7178	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7819	Suspended
0.7175	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1608	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6959	Discontinued
0.7115	Intermediate Similarity	NPD6674	Discontinued
0.7105	Intermediate Similarity	NPD5735	Approved
0.7099	Intermediate Similarity	NPD4380	Phase 2
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7097	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6005	Phase 3
0.7097	Intermediate Similarity	NPD6004	Phase 3
0.7097	Intermediate Similarity	NPD6002	Phase 3
0.7097	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD1778	Approved
0.7083	Intermediate Similarity	NPD5711	Approved
0.7083	Intermediate Similarity	NPD4626	Approved
0.7078	Intermediate Similarity	NPD7033	Discontinued
0.7073	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.7067	Intermediate Similarity	NPD7095	Approved
0.7063	Intermediate Similarity	NPD9545	Approved
0.7052	Intermediate Similarity	NPD6559	Discontinued
0.7032	Intermediate Similarity	NPD2531	Phase 2
0.7029	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5951	Approved
0.702	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3818	Discontinued
0.7014	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5691	Approved
0.7012	Intermediate Similarity	NPD6801	Discontinued
0.7012	Intermediate Similarity	NPD1934	Approved
0.7006	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3882	Suspended
0.6987	Remote Similarity	NPD2346	Discontinued
0.6987	Remote Similarity	NPD7266	Discontinued
0.698	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4198	Discontinued
0.697	Remote Similarity	NPD1465	Phase 2
0.6966	Remote Similarity	NPD4059	Approved
0.6966	Remote Similarity	NPD5125	Phase 3
0.6966	Remote Similarity	NPD5126	Approved
0.6966	Remote Similarity	NPD17	Approved
0.6964	Remote Similarity	NPD5494	Approved
0.6959	Remote Similarity	NPD6696	Suspended
0.6928	Remote Similarity	NPD943	Approved
0.6928	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2490	Approved
0.6927	Remote Similarity	NPD2488	Approved
0.6923	Remote Similarity	NPD4477	Approved
0.6923	Remote Similarity	NPD4476	Approved
0.6923	Remote Similarity	NPD2935	Discontinued
0.6919	Remote Similarity	NPD7177	Discontinued
0.6908	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7985	Registered
0.6906	Remote Similarity	NPD3022	Approved
0.6906	Remote Similarity	NPD3021	Approved
0.6901	Remote Similarity	NPD6166	Phase 2
0.6901	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1651	Approved
0.6894	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2342	Discontinued
0.6882	Remote Similarity	NPD3787	Discontinued
0.6879	Remote Similarity	NPD7635	Approved
0.6875	Remote Similarity	NPD3300	Phase 2
0.6875	Remote Similarity	NPD7236	Approved
0.6867	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2801	Approved
0.6864	Remote Similarity	NPD4666	Phase 3
0.6863	Remote Similarity	NPD6233	Phase 2
0.6859	Remote Similarity	NPD2799	Discontinued
0.6859	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7685	Pre-registration
0.6855	Remote Similarity	NPD3400	Discontinued
0.6855	Remote Similarity	NPD3750	Approved
0.6849	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7411	Suspended
0.6848	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8651	Approved
0.6845	Remote Similarity	NPD8319	Approved
0.6845	Remote Similarity	NPD3749	Approved
0.6845	Remote Similarity	NPD8320	Phase 1
0.6842	Remote Similarity	NPD7008	Discontinued
0.6839	Remote Similarity	NPD4097	Suspended
0.6831	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3817	Phase 2
0.6824	Remote Similarity	NPD9269	Phase 2
0.6821	Remote Similarity	NPD2861	Phase 2
0.6818	Remote Similarity	NPD826	Approved
0.6818	Remote Similarity	NPD825	Approved
0.6813	Remote Similarity	NPD6534	Approved
0.6813	Remote Similarity	NPD6535	Approved
0.681	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5709	Phase 3
0.6797	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7097	Phase 1
0.6792	Remote Similarity	NPD2800	Approved
0.6791	Remote Similarity	NPD7435	Discontinued
0.679	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8151	Discontinued
0.6788	Remote Similarity	NPD7028	Phase 2
0.6786	Remote Similarity	NPD7768	Phase 2
0.6786	Remote Similarity	NPD4750	Phase 3
0.6779	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5327	Phase 3
0.6774	Remote Similarity	NPD2494	Approved
0.6774	Remote Similarity	NPD2493	Approved
0.6768	Remote Similarity	NPD7239	Suspended
0.6766	Remote Similarity	NPD5761	Phase 2
0.6766	Remote Similarity	NPD5760	Phase 2
0.6755	Remote Similarity	NPD4582	Approved
0.6755	Remote Similarity	NPD5647	Approved
0.6755	Remote Similarity	NPD4583	Approved
0.6752	Remote Similarity	NPD7305	Phase 1
0.6752	Remote Similarity	NPD651	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data